Question

My email server requires TLS (SSL) to connect and send mail. We are still running version 4.x. Is there a way to configure the system to handle SMTP over SSL with TLS?

Answer 1

Maybe with an SSL tunnel. i.e. you could set up a tunnel on your machine to your SMTP server and then have FogBugz connect to the local tunnel.

FogBugz 7 supports this though. You could just upgrade...

Answer 2

These steps are for FogBugz 7 implicit SSL, but they may work for you to setup the tunnel you need. Upgrading FogBugz is still easier though ;)

Follow the instructions here, but use these lines in your config:

[SMTP FogBugz]

accept = 1099

connect = [smtp server]:[smtp port - usually 465]

1. Verify that Stunnel is working using telnet:

   1. From a command line, run "telnet localhost 1099". You should see something like "220 [smtp-server]".
   2. In telnet, type "starttls". You should see something like "554 5.5.1 Error: TLS already active"

2. In FogBugz, go to Admin > Site (Settings > Site for FogBugz < 7)

3. Set the SMTP server to "localhost" and the port to 1099

4. Uncheck the "Use SSL" box

Answer 3

The above worked for me when configuring for Google Apps, but I didn't get the same response when testing stunnel. I was able to open the telnet connection and get a response from the other end of the tunnel, but when I tried to send the "starttls" command I got:

502 5.5.1 Unrecognized command. 4sm12846050qwe.57

But otherwise everything worked fine, once I just decided to skip that step and run the diagnostic within Fogbugz to test it. My stunnel.conf file is this:

client = yes
output = stunnel-log.txt
debug = 0
taskbar = yes

[SMTP Gmail ]
accept = 1099
connect = smtp.gmail.com:465

[POP3 Gmail ]
accept = 108
connect = pop.gmail.com:995